diff --git a/packages/tree-extension/src/index.ts b/packages/tree-extension/src/index.ts
index 045e79bdb..359e3bc40 100644
--- a/packages/tree-extension/src/index.ts
+++ b/packages/tree-extension/src/index.ts
@@ -32,8 +32,16 @@ import {
 
 import { Menu, MenuBar, TabPanel } from '@lumino/widgets';
 
+/**
+ * The file browser factory.
+ */
 const FILE_BROWSER_FACTORY = 'FileBrowser';
 
+/**
+ * The file browser plugin id.
+ */
+const FILE_BROWSER_PLUGIN_ID = '@jupyterlab/filebrowser-extension:browser';
+
 /**
  * Plugin to add extra commands to the file browser to create
  * new notebooks, files, consoles and terminals
@@ -101,7 +109,7 @@ const browserWidget: JupyterFrontEndPlugin<void> = {
     app: JupyterFrontEnd,
     factory: IFileBrowserFactory,
     translator: ITranslator,
-    settings: ISettingRegistry,
+    settingRegistry: ISettingRegistry,
     toolbarRegistry: IToolbarWidgetRegistry,
     manager: IRunningSessionManagers | null
   ): void => {
@@ -135,7 +143,7 @@ const browserWidget: JupyterFrontEndPlugin<void> = {
       browser,
       createToolbarFactory(
         toolbarRegistry,
-        settings,
+        settingRegistry,
         FILE_BROWSER_FACTORY,
         browserWidget.id,
         translator
@@ -151,6 +159,19 @@ const browserWidget: JupyterFrontEndPlugin<void> = {
       tabPanel.tabBar.addTab(running.title);
     }
 
+    // show checkboxes by default if there is no user setting override
+    const settings = settingRegistry.load(FILE_BROWSER_PLUGIN_ID);
+    Promise.all([settings, app.restored])
+      .then(([settings]) => {
+        if (settings.user.showFileCheckboxes !== undefined) {
+          return;
+        }
+        void settings.set('showFileCheckboxes', true);
+      })
+      .catch((reason: Error) => {
+        console.error(reason.message);
+      });
+
     app.shell.add(tabPanel, 'main', { rank: 100 });
   }
 };
diff --git a/ui-tests/test/mobile.spec.ts-snapshots/tree-chromium-linux.png b/ui-tests/test/mobile.spec.ts-snapshots/tree-chromium-linux.png
index 0a0d2151d..7bee71a56 100644
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diff --git a/ui-tests/test/mobile.spec.ts-snapshots/tree-firefox-linux.png b/ui-tests/test/mobile.spec.ts-snapshots/tree-firefox-linux.png
index 7f0e20256..15c4741a1 100644
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diff --git a/ui-tests/test/settings.spec.ts-snapshots/top-hidden-chromium-linux.png b/ui-tests/test/settings.spec.ts-snapshots/top-hidden-chromium-linux.png
index 06a75207c..7599338fa 100644
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diff --git a/ui-tests/test/settings.spec.ts-snapshots/top-hidden-firefox-linux.png b/ui-tests/test/settings.spec.ts-snapshots/top-hidden-firefox-linux.png
index a5533f544..e3f9f4621 100644
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diff --git a/ui-tests/test/settings.spec.ts-snapshots/top-visible-chromium-linux.png b/ui-tests/test/settings.spec.ts-snapshots/top-visible-chromium-linux.png
index f4d7b1cde..384881c83 100644
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diff --git a/ui-tests/test/settings.spec.ts-snapshots/top-visible-firefox-linux.png b/ui-tests/test/settings.spec.ts-snapshots/top-visible-firefox-linux.png
index 0f68636d7..bdcbea587 100644
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